diff --git a/.changeset/generated-at-any-depth.md b/.changeset/generated-at-any-depth.md
new file mode 100644
index 00000000..0440245c
--- /dev/null
+++ b/.changeset/generated-at-any-depth.md
@@ -0,0 +1,11 @@
+---
+"@taskless/cli": patch
+---
+
+The deprecated-path guard now skips `generated/` at any depth.
+
+`typeScriptSources` excluded only a top-level `src/generated`, so a nested
+generated directory would have had every deprecated path in its transcript
+reported as a call site. The exclusion exists because a generated directory is
+the schema's own transcript rather than a call site, and that reasoning does not
+depend on how deep it sits.
diff --git a/packages/cli/test/api-deprecated-paths.test.ts b/packages/cli/test/api-deprecated-paths.test.ts
index 61fcffa0..be97e040 100644
--- a/packages/cli/test/api-deprecated-paths.test.ts
+++ b/packages/cli/test/api-deprecated-paths.test.ts
@@ -58,8 +58,12 @@ async function typeScriptSources(directory: string): Promise<string[]> {
     .map((entry) => join(entry.parentPath, entry.name))
     .filter(
       // `generated/` is the schema's own transcript: it necessarily names every
-      // path, deprecated ones included, and is not a call site.
-      (file) => !relative(directory, file).startsWith(`generated${sep}`)
+      // path, deprecated ones included, and is not a call site. Matched at any
+      // depth, because that reasoning is about what a generated directory IS
+      // and does not depend on where it sits. `startsWith` reached only a
+      // top-level `src/generated`, which is a no-op today and would have
+      // reported a nested one as a wall of false offenders.
+      (file) => !relative(directory, file).split(sep).includes("generated")
     );
 }